The Drivelous Purgatory of School
by Insanely-Yours96
Summary: Highschool AU. Castiel and Anna Novak are the new kids in school, with weird habits and rich, private school backgrounds. Dean's the run ragged kid working two jobs to provide for himself and Sammy. Bobby's the cranky homeroom and shop teacher, Ellen runs a kickass bar, and Ash is still... well, Ash.


"Class, this is Anna Novak," he faintly hears Bobby say over the insistent pounding in his ears. God, it was like a hangover without the fun of the night before. "You can take the seat next to Dean—_Winchester_, you idgit, sit up, this class ain't for you to sleep in."

"Could've fooled me," he groans half-heartedly, pushing himself into a sitting position with his elbows and blinking to adjust to the too-bright fluorescent lighting the room has to offer.

He shoots a glare to his left where a chair is loudly scraping its way across the floor, and then stops. Dean recoils, as if slapped, because, wow, she—Amy? Annie?—is the most ridiculously attractive woman he's ever seen, and that's saying a lot, because he's met thousands of beautiful women with all his moving around. She's absolutely stunning, with curled dark red hair, somewhere between short and long, fitted jeans, and a green halter top that doesn't leave much to the imagination. She swings a small leather jacket over the back of her chair before sitting gracefully, crossing her legs and shooting him a mysterious little smirk.

"Winchester," she says as their eyes meet. Hers are blue, very blue, and surrounded by coal black eyeliner and lash-lengthening mascara. Dean suspects she'd look just as pretty without the makeup, because she's got bone structure to die for, full red lips, and, _fuck_, she's hot.

"Amy," he says back, because he thinks that's it, but if the arch in her brow is anything to go by, it isn't, so he just groans and turns away, letting his head fall back to the table with a loud 'thump' and murmuring something that sounds suspiciously like "way too fucking early for this shit".

* * *

Strangely enough, he doesn't have to make the first move on Anna, because he's sitting under a tree, bored and still nursing a killer headache, when she comes up and plops down next to him.

"This'll help," she says smoothly, tossing him a purple pill bottle. "Take two."

Dean looks at the bottle skeptically for a long moment, but then the killer pain in his head seems to spike so he gives a _fuck it_ shrug and pops two capsules into his mouth. Five minutes later his headache is almost completely gone. He pushes himself up from the grass that he'd lazily collapsed onto and pushes his sunglasses to the top of his head.

"I love you," he declares reverently. She looks from the clear sky to him, quirks an amused brow, and takes that as an invitation to steal some fries from his lunch tray.

They eat in a companionable silence for a while, and then Dean starts quizzing her on her taste in music. When she says something about liking Ke$ha's latest song he sort of flips out and drags her to his beloved '67 Impala, shoves his AC/DC cassette in, and makes her listen to some "real music". When he goes on to play some of his favorite Blue Oyster Cult, Metallica, Led Zeppelin, and Bon Jovi songs, she makes fun of him for being stuck in the 80s, but her taste isn't total crap, because she knows half the songs and sings along. He laughs at her terrible rendition of "Back in Black" and tells her he should really keep her voice to herself. She punches him in the arm and grumbles something about him being tone-deaf.

They both get so caught up in talking and listening to the music that they don't hear the bell when it goes off, signaling the end of lunch, and end up just chilling in the Impala until Dean's phone buzzes with a text from Jo asking where the fuck he is. It's already thirty minutes into the next period, and Dean curses and quickly tells Anna where to find her next class. When they'd moved this last time around Sam had made Dean promise to attend all his classes, and Dean wasn't one to break promises to his little brother.

He jogs to his Lit class and manages to get there just as Mrs. Roberts is finishing up a lecture and asking for homework. He has to spend almost three full minutes apologizing before she'll let him sit down, and even then she assigns a detention along with two extra pages to his homework. He winces and knows that he'll have to stay late to try and talk her out of the detention, because he has work right after school, and if he's late he could get fired. He'd already been written up for taking Sammy to the emergency room last month after he'd fallen and sprained his wrist at school—Dean suspects a bully was the actual cause, but Sam wouldn't admit anything.

As soon as he sits down in his usual seat Jo tosses a paper at the side of his head demanding to know why he was late. He just scowls at her and starts annotating his copy of _Romeo and Juliet_, trying to show Mrs. Roberts she's got his full attention, even though this is at least the fifth time he's annotated this book for different high schools and he could probably do it in his sleep. His feigned attention lasts all of ten minutes, when she says, "Mr. Novak, can you tell me what he means when he says '_Take thou some infection to thy eye, And the rank poison of the old will die'_?"

"I think," a deep, rumbling voice says from right being Dean, and he jumps and turns to stare over his shoulder, wondering how he hadn't noticed that somebody had taken the normally vacant seat behind him. The guy is obviously a new student, and probably Anna's brother, or something, seeing as Mrs. Roberts called him "Mr. Novak". He looks pretty formal, clothed in a dark blue button up, black slacks, and dress shoes, but his hair is a dark rumpled mess, like he just left it how it was after he rolled out of bed. What catches Dean's attention, though, are his eyes, the same startling blue as Anna's, maybe even brighter and clearer. They're locked on Dean's own eyes, even as he goes on speaking in his deep, chain-smoker voice, answering Mrs. Roberts's question.

Dean, despite being surprised by the attention, doesn't even blink in the face of the teens unwavering gaze, and just stares right back until Mrs. Roberts snaps, "Very good, Mr. Novak. _Winchester_, since you decided to grace the class with your presence, do you think you might _pay attention_?"

Dean doesn't even flinch at the harsh tone, having come to expect it, and turns from the Novak (still staring) to look at Mrs. Roberts, who is scowling at him darkly. He blinks at her, and says, in his least patronizing tone, because he still has to talk himself out of a detention, "I was paying attention, ma'am."

"Oh?" she says skeptically, "Then perhaps you can tell us your take on Romeo's next few lines?"

Dean shrugs, and does, flawlessly translating the old Shakespearian words into terms that his fellow classmates can easily understand. By the time he's done Jo's stifling laughter behind her hand and Mrs. Roberts is staring at him is blatant disbelief. She even goes so far as to come to his desk, snatch up the assigned reading, and scan the next few annotated pages of his book.

"This section hasn't even been assigned, Winchester," she says, sounding a little awed as he just shrugs again.

"Sorry, just thought I'd get ahead."

"Well," she clears her throat and hands the script back. "That's not a problem. It seems very thorough—I'm glad you came prepared, though it will do you well not to be late again."

_Jesus_, Dean thinks, annoyed, _she acts like it's the hundredth offense rather than the first_. Instead of voicing his thoughts, he just says, "Of course, ma'am."

She nods, goes back to the front of the room, and chooses different people to translate the reading for the remaining five minutes of class. Jo indiscreetly holds her hand out for a fist bump, and he rolls his eyes and ignores her.

He has the strange urge to turn around and start a staring match with the guy behind him again, but it'd probably just make Mrs. Roberts pissy, so he refrains and absently follows along with Chuck's stuttered translation of the beginning of Act 1, Scene III.

Once the bell rings and they're dismissed, Jo's right at his side, saying, "So are you going to answer me? Why were you late?"

Jo's a cute blond with dimples and pretty much his only friend. She's the daughter of Ellen, the owner of the bar he's works at on weekends and after his hours at the gas station. Ellen and Jo both know about the situation with his dad and Sammy, and Ellen spares him shifts whenever she can to help him pay for rent and food.

At the start of their tentative friendship she had a huge, obnoxious crush on him that lasted about a week. It was really awkward, because he didn't want to screw up with arrangement with Ellen by dating her daughter, and Jo wasn't really Dean's type, because he actually _liked_ her, and Dean only dated convenient, vapid girls that wanted him for his body. And even then, it wasn't really 'dating', it was more like fuck-buddies. Anyway, all in all, Jo was way better as a friend than a conquest—and, come to think of it, as hot as Anna is, she'll probably end up as a friend, too, because he really likes her, and he doesn't do the whole boyfriend/girlfriend thing.

"We can talk at the Roadhouse later," he tells her. _The Roadhouse_ is the name of Ellen's bar, and she'd promised him a shift. "I need to talk to Mrs. R real quick. She's got me down for detention."

"Yeah," Jo says, making a face. "I heard. She's really got it out for you, huh?"

Dean just shrugs, so Jo rolls her eyes, takes the hint, and says, "Later, loser," before heading out the door along with the rest of the class.

Dean turns to shove his copy of _Romeo and Juliet_ in his bag and is surprised to see the Novak guy still sitting at his desk, watching Dean with a tilted head. Dean watches him back for a second, and almost tilts his own head to the side, before catching himself and giving a half-smile and nod. The guy just tilts his head more in response, so Dean grabs his bag and heads over to the teacher.

"Yes, Winchester, what can I do for you?" she asks warily as soon as she spots Dean approaching, and Dean turns on the charm, giving her a small smile and rubbing the back of his neck.

"Look, Mrs. Roberts, I'm really sorry for coming in late, and I know there's no excuse, but is there any way I can get out of my detention? I pick up my kid brother every day after school and then I barely have time to drop him off at home before I need to be at work."

Mrs. Roberts frowns at him. "If you didn't want detention, Mr. Winchester, you shouldn't have skipped the first thirty-five minutes of my class. I'll admit, your homework is 'A' material, but half of the time you sleep in my class. Your annotations are fantastic, but you don't apply yourself, and I do not stand up here every day to hear myself speak. I'm sure one of your parents can pick your brother up from school, and it's only an hour's detention—I think I'm being reasonable, considering."

Dean takes a deep breath and nods, trying to quell the urge to scream at the woman that he works over forty hours a week on top of taking care of Sammy and getting under three hours of sleep, so _of course_ he sleeps in her boring goddamn class. "I understand that, Mrs. Roberts, and I'm sorry, I know sleeping in class is unacceptable. Again, no excuses, but there is nobody else who can pick Sammy up and if I'm late to work I may get fired."

"It's hard to believe that neither of your parents can take time off work to pick your brother up, Dean, and I'm sure if you call in to work and say you'll be late they won't fire you. It isn't like there is any reason for a seventeen year old to have a job, anyway."

Profanities are on the tip of Dean's tongue, so he bites it, takes another calming breath, and tries to ignore his clenching fists and quickly rising temper.

"My mother's not in the picture and my dad can't take calls at work, ma'am." _Mom's dead and dad's probably drunk off his ass a few states away_. "Can I do anything instead of the detention? I can write five extra pages for the homework?"

Mrs. Roberts stares at him through narrowed, suspicious eyes. "I've already assigned you two extra pages, Winchester, and I'm not sure it's possible to expand one act so much. Plus, the more you write, the more I have to grade."

Dean drops his smile, which probably looks noticeably forced by now. "I can serve a detention during lunch, or I can write the ten pages for two acts, or I can organize the—"

"Mr. Winchester, this is _ridiculous_. I really don't see why you can't just—"

"Excuse me, Mrs. Roberts," a low voice interrupts, and Dean spins around, surprised, to see that the Novak guy is actually _still_ in the room, standing right behind him, _way_ to close—personal space, anyone?—looking at Mrs. Roberts with big, earnest blue eyes. "But you said I'd need a tutor to get caught up with your class's curriculum. Perhaps Dean can do that in place of his detention? After all, I didn't fully understand a few of the concepts you were going on earlier in the class, like—"

Dean's already stopped hearing by now, his mind stuck on _tutor_. After years of being lied to, he's pretty much built a bullshit detector, and whatever the Novak is spewing on about while looking all earnest and crap, it is definitely bullshit. The gleam in his eye and persuasive lilt of his voice tells Dean everything he needs to know.

Mrs. Roberts, however, seems utterly unaware of the maelstrom of lies, because she's nodding slowly, looking like she's actually contemplating what's being said.

After about twenty straight seconds of talking (lying), the guy finally stops and meets Dean's eyes, and all Dean can think is _holy shit, he's good_.

After a few seconds he gets a frown and head tilt, and the guy is obviously waiting for something, so Dean turns back to Mrs. Roberts, fixes an easy smile on his face, and shrugs. "I'm fine with it if you are, Teach."

"Are you sure, Castiel? Have you two even properly met?" Mrs. Roberts asks, looking less skeptical and more hopeful, like, _thank God, I can get two problems off my back at once_.

_Well, at least I've finally got a name,_ Dean thinks as the Novak shrugs, looking, for the first time, a little out of his depth. What could that mean? _He can lie easy as pie but socializing is too difficult?_

Dean holds in a tired sigh and grins, flinging an arm over Castiel's shoulder. "Come on, Mrs. Roberts, I'm sure me and Cas'll get along just fine. You're a pretty cool guy, right, Cas?" Dean asks, throwing a wink to the stiff, unresponsive, slightly shocked-looking man beside him.

"I…" Castiel says, and Dean gently pinches his arm. He hesitates for another second, then slowly nods, draping his own arm awkwardly over Dean's shoulder. "Of course, Dean. I am sure I will catch up rapidly if you are available to tutor me."

Dean grins at him. "And I am. So, Mrs. Roberts, this an acceptable substitution for my detention? I think the bell is about to ring and we really need to be getting to class."

"Well," she starts, just as the bell rings, signaling the start of the next class. Dean knows she has a free period, thus why no students are piled into the room. "I guess that would be okay…"

"Great!" Dean says, dropping his arm from around Castiel, who immediately does the same and shifts his weight awkwardly. "Would you like me to show you to your next class real quick, Cas, or do you know where it is?"

"Oh, well, I should be able to find it, you don't have to trouble—"

"Hey, no problem," Dean interrupts, steering him towards the door. "We might as well be friends, right? I'll be tutoring you, after all."

Castiel nods hesitantly, and Dean smiles back at Mrs. Roberts, who looks sort of confused. "Don't you boys forget to—uh—plan out the times," she calls after them as they get to the doorway.

"Of course!" Dean says, and then shuts the door behind him. He sighs as soon as it _click_s and his entire body sags wearily. He feels absolutely exhausted and the headache from earlier seems to be coming back with vengeance.

"Dean?" Castiel's low voice asks from behind him, and Dean turns to see big blue eyes watching him. They look almost worried, and Dean lets a slow, real smile spread across his face, unbelievably grateful to this stranger—Castiel.

"Hey, thanks a lot, man, that was a really cool thing to do. I'd be toast if you hadn't come up with that whole tutoring thing."

Castiel, who is already standing there all stiff and awkward, seems to become tenser at his words, and his entire expression (a small frown and crease between the brows) seems to shudder before vanishing into a blank mask. "It isn't a problem, Dean," he says, and then just turns and walks away.

Dean blinks after him for a long moment, confused, before saying, "Whoa, _what_?" and jogging to catch up.

"Hey, wait up," he calls, and Castiel stops dead just before turning the corner. Dean's glad he was jogging instead of flat out running, because otherwise he'd probably of run straight into him.

"I thought I was going to show you where your class was?" he asks as he comes to a stop, putting a hand on Castiel's shoulder and turning him a bit so they're standing face-to-face instead of face-to-side. Castiel just stares at him blankly and tilts his head in what Dean guesses must be confusion. He takes a half step back, feeling suddenly really lame, and shrugs, scratching the back of his neck like he's reflexively done for years when he thinks he's about to be scolded. "I mean, it's cool if you want to find it on your own or whatever. I just thought I was going to… you know… help you out."

Castiel just keeps staring at him for a long moment, his head tilting even more, before he says, very softly, "Oh."

"Oh?" he says back, lips curling upward by their own volition. "Is that an, "Oh, okay, sure", or an "Oh, I don't need your help, leave me the fuck alone"?"

Castiel blinks at him, very slowly, a crease forming between his brows. "More of the first one, I think," he finally says.

Dean stares at him for a second, then grins, and nods. "That's good," he says, "Who do you have?"

Castiel chews his (very pink) lower lip and looks down thoughtfully. "After Mrs. Roberts I believe it was Mr. Carter, Study Hall, Room 29."

"Oh, hey, I have that now, too," Dean grins. "Only gotta go to one place."

Then, after a second, "Wait, did you memorize your entire schedule?"

Castiel nods. Dean stares. "Seriously, Cas? That's amazing! I can hardly remember things for five minutes. Usually gotta carry my schedule around for the first three days every time I switch schools."

Castiel stares at Dean, not saying anything. Dean shifts uncomfortably and wrinkles his nose. "Is having a bad memory that bad?"

Castiel shakes his head, the crease reappearing between his brows. "No, it isn't that. It's just… you're still calling me Cas."

Dean blinks and tilts his head a bit to the side, unwittingly copying Castiel's gesture of confusion. "Oh, I'm sorry. If you don't like it, I can stop—"

"No," Castiel interrupts, frowning. "It's—nice."

Dean snorts and shakes his head, clapping Castiel on the shoulder. "Well, okay then. If it's _nice_."

Castiel tilts his head. "You're teasing me," he states.

"Well, yeah," Dean says, grinning at him. "That's what friends do, right? Now come on, we're already late, and I don't want to talk myself outta another detention. Not that Mr. C would ever give out a detention, 'course—he's a pushover."

* * *

Mr. Carter doesn't care what you do during Study Hall, so Dean and Castiel just hang out the entire time and talk (though it takes a while to convince Castiel that no, he doesn't have to get out his homework and do it right this minutes unless he wants to). Dean finds out that Anna is Castiel's half-sister, and they didn't know each other until four years ago, but now they're pretty close. They're family is super rich, so this is Castiel and Anna's first time in public school (they both went to same-sex boarding schools before) and they recently moved from California to live with their older brothers (also only half-siblings—Castiel's dad really got around) Gabriel and Michael.

Dean discovers Castiel's sense of humor sometime during those fifty-minutes. It's sort of hard to tell when he's kidding, because his humors pretty dry and he has a poker face like nobody's business, but Dean's always been pretty good at reading people, and his job at Ellen's bar required him to lend a listening ear, so he can basically recognize what different voice-pitches mean.

Castiel gets Dean talking about his job at the gas station, and he ends up ranting about what an asshole his boss is, and thanks Castiel again for saving him from getting fired. He talks about Sammy a lot, knowing that he sounds like a proud mother, but not really caring. Sam's a really smart kid, and is going to do some big things someday—he can feel it. When Castiel asks about his dad, he sort of shuts down, and changes the topic. Castiel doesn't mention it.

Dean notices Castiel has a habit of staring a lot, but he doesn't really mind, and just stares right back as they talk. At one point Castiel mentions that all the other students seem uncomfortable around him, and asks why. Dean tells him it's because of his odd habits and the way he's dressed.

"What's wrong with the way I'm dressed?" Castiel asks, looking down at his outfit. "I like it."

Dean grins. "Me too, but most guys in high school just wear jeans and t-shirts. Guess you just look a little dressed up. Nothin' wrong with that, though. It's just… different."

By the time class is over, they know a good deal about each other, and feel more like friends than awkward acquaintances. Castiel even smiles at him before they part ways, which he feels is a rare occurrence, even though he's barely known the guy for an hour.

* * *

**A/N: So I wrote this quite some time ago, and if it gets a good response I guess I'll continue it. Hope you enjoyed.**


End file.
